Or both. In 1996, Kaszak, then a state representative, lost a congressional primary to fellow state representative Rod Blagojevich. In 2002, when Blagojevich ran for governor, Kaszak tried again. That time, her opponent was Rahm Emanuel.

Emanuel had moved to Ravenswood just three years before, to work as an investment banker, so Kaszak attempted to portray him as a D.C. carpetbagger.

“I’m from here,” Kaszak asserted in her ads, as she drove her Dodge Intrepid through the bungalow belt. Emanuel was shown sitting in the back seat of a limo, talking on a cell phone. Kaszak also leaned on her ethnic roots to connect with the district’s large Polish population.

But Emanuel had powerful patrons. Then, as now, Bill Clinton came to Chicago to campaign for Emanuel. And then, as now, Mayor Daley was behind Emanuel’s campaign. Daley’s patronage chief, Robert Sorich, and his water department head, Donald Tomczak, both dispatched city employees to walk precincts for Emanuel. Both went to prison after being convicted of handing out jobs and promotions for political work.

“In the indictment of Sorich, he indicated that one of the things that he did was to bring in city workers to work for Rahm in my race,” Kaszak says. “On Election Day, when I went from poll to poll to greet the voters and talk to workers, there were a lot of people in those precincts that I didn’t recognize, and when I talked to them, many of them were from the suburbs. I suspect some of them might have had relationships with city contractors.”

That night, when Kaszak asked her campaign manager why she’d lost, he had a two word answer: “The M and Ms: money and the mayor.”

“Rahm is tough, there’s just no doubt about it,” Kaszak says. “He has huge fundraising capacity, as we’re seeing right now. I consider myself to be a good fundraiser, but he takes it to a whole nother level, in Hollywood, Manhattan, California. And he has all these relationships from these national campaigns he’s been on, and I certainly didn’t have that. And he works very hard, and he’s a bright guy. He’s familiar with a lot of issues.”

Kaszak has no complaints about Emanuel’s performance as a congressman -- he even hired a Polish-speaker staffer for his district office, she says. But she has another candidate in the mayor’s race. On Sunday, she appeared at a press conference in Eckhart Park to endorse Gery Chico. Both worked for the city in the 1980s: Chico at the planning department and the Finance Committee, Kaszak as General Attorney for the Park District.

“When I saw what the choices are, it was so clear to me I was going to support Gery, because he was somebody who has, for decades, been working on issues in the city,” Kaszak says. “I just think you need that intimate knowledge of what’s going on in the communities, in order to make the right decisions for people.”

As the politician ever to seriously challenge Emanuel, what advice does Kaszak have for Chico? Play up your neighborhood roots.

“I think what Gery needs to do is connect with all of his friends in these neighborhoods that he’s been working with for 25 years and remind them how good he has been in listening to them and doing some things about the concerns that they have,” she says.

Also, raise lots of money. Chico can never raise as much money as Emanuel, but she thinks he can raise enough to win the election.

“There’s a threshold,” she says. “You have to have a certain amount of money in order to be a credible candidate. It’s going to take millions.”

Buy this book! Ward Room blogger Edward McClelland's book, Young Mr. Obama: Chicago and the Making of a Black President , is available Amazon. Young Mr. Obama includes reporting on President Obama's earliest days in the Windy City, covering how a presumptuous young man transformed himself into presidential material. Buy it now!